Jess's Contemplation
by MountaineerTookieClothespin
Summary: First chapter is from Jess's point of view about himself, the town, adn Rory. Rory and Jess's thoughts on each other and how they feel. Please R&R! J&R! Chapter 3 uploaded!
1. Small Town

Disclaimer: I do not own anything pertaining to the Gilmore Girls show or any of the characters.

"Luke, I'm going out." I holler as I thump down the stairs.

"Fine, but be back in time for closing." My Uncle Luke hollers back as I sweep past him and out the front door.

Stopping a few feet from the diner's door, I slowly gaze around this hokey town that the locals call Stars Hollow. It's like something out of a sixty's sitcom. Not my kind of town at all.

The town locals are very proud of their tiny town. Not that I would know or care.

Of course I've been here about a year now, but I will never call myself a town local.

That isn't me and never will be.

"I'm a lone wolf, someone you wouldn't want to encounter after dark. Someone who's not good in school or at making friends.

It's not that I couldn't be good at school; it's just that I don't want to be good at schoolwork.

My Uncle Luke probably thinks that I have no social skills and that I'm a troublemaker with a bad attitude.

In fact pretty much everyone in this hick town thinks that I'm a troublemaker with a bad attitude and no good inside of me.

That is, everyone but a certain Lorelai Leigh Gilmore.

Everyone calls her Rory. That's her nickname. And I can't explain it, but Rory suits her a lot better than Lorelai ever will.

Maybe it's because when I think of the name Lorelai, I always associate it with Rory's annoyingly peppy mother, who hates my guts.

She thinks the same as everyone else in this town. That I'm a bad egg with no heart and that I'll end up hurting her daughter.

But I won't hurt Rory, no one will, not if I have anything to say about it.

But of course I really don't have any say in the matter, not while Rory's annoyingly tall, bag boy, boyfriend stands in my way.

He's like some bad brick wall, that's keeping me from Rory.

Although, I don't think that's she'll be with him for very long.

It's seemed lately that he's been getting a little too possessive and bossy for Rory's taste.

Who knows, though? She's probably way to loyal to dump him over that.

Sighing, I wake up from my daydream and head off for my favorite spot in Stars Hollow.

Hard to believe, huh? I actually have a favorite spot in Stars Hollow.

But it's not just any spot, it's what I like to privately think of as, Rory's and my spot.

It's where we had our first unofficial date. Maybe the only date that I'll ever have with her.

I took her there for a picnic after I outbid Dean in the basket sale, that the town puts on every year.

Man he was furious. It's one of my favorite memories so far.

Well, that one and the one, when I first saw Rory.

Anyway, my favorite spot in Stars Hollow would be the bridge, which is where I'm headed now.

It's where I go to be alone, or to think, or to just relax and read a book.

I think that that's one of the main reasons that Rory seems to be attracted to me. Because I read a whole lot, and so does she.

I'm almost to the bridge now. And then, suddenly, I'm there and my foot is taking the first step onto the old wooden bridge.

I love the way my footsteps have that hollow ring as I walk across it to get to my usual reading spot. Smack in the middle of the bridge with my feet hanging over. That's where I sit.

But this afternoon, my spot is taken. And the person in my spot is reading a book and dangling her legs over the edge.

There's only one person that it could be and her name is Rory Gilmore. The one person in Stars Hollow who actually understands me.

A/N: So, what did you guys think? Please leave a review and let me know. Please keep all reviews G rated with no implied, bleeped out with stars, or actual cuss words! Thanks a lot!


	2. The Bridge

Disclaimer: I do not own anything that pertains to the Gilmore Girls show or any of the characters or products.

I was so engrossed in my book that I didn't hear the footsteps until they stopped right behind me.

Slowly, I turned around and looked up into Jess's clear brown eyes.

He smirked at me and said, "Hey."

I gave a small smile. "Hey back."

For a few minutes no one spoke. Then Jess suddenly said, "You're in my spot."

I gave him a confused look. "What?"

"You're in my spot." Jess replied.

"What are you talking about?" I asked, still bewildered.

"That is the spot where I always sit, and your sitting there."

I just grinned at him. "Is that so?"

"Yes, it is. But just this once I will let you sit there and I'll sit beside you." Jess said in a mock gracious tone.

I just laughed and picked my book back up. But no matter how hard I tried I just couldn't concentrate on the words before me.

All I could think about was the guy sitting beside me. Over and over my mind kept replaying the first time I had ever seen Jess. I was sitting at my desk doing homework when I looked up and he was standing there. Something about him instantly made me know that I wanted to be his friend. That I desperately wanted him to like it here in Stars Hollow.

At first I hadn't even been remotely attracted to him. I only thought of him as my good friend Jess. But then… as I got to know the real Jess… the Jess that no one else knew. I slowly felt myself falling in love with him. But I knew that it couldn't work out. Lorelai, the person I'm closest to doesn't care for him at all. And he would not only be my boyfriend and perhaps future husband, but possibly her future son-in-law. Plus, there's that little thing called my current boyfriend, Dean. I do love Dean, in a way, but not the way that I love Jess. I could see myself marrying Jess and spending the rest of my life with him. I don't see Dean that way at all. I could see being friends with Dean but not marrying him. But over and over I've asked myself, how could I dump Dean and start dating Jess? Is it worth the risk of dating him and finding out that we can only ever be friends? Is it worth losing his friendship over if it didn't work out? Could I possibly, potentially stick Lorelai with a son-in-law she despises? I knew that if I broke up with Dean that he would eventually move on and find someone else. But I'm just not sure if I can risk giving up a relationship that I'm comfortable and happy in for the unknown.

I didn't realize that as I sat pondering this, that Jess also was thinking along the same lines.

Jess's pov…

I wish that she would just give him up. Let him move on and find someone who really loves him. I wish that she would stop worrying about it and just dump him. I know she loves me. Oh sure, she hasn't said it out loud yet, but I can see it in her eyes. If she would only tell me that she does then I would ask her to marry me. But I can't tell her that. It has to be her decision to break up with Dean. I mean I could even stomach having Lorelai as a mother-in-law if Rory would only marry me. I love her. We couldn't get married right away, because we're to young, but I could go ahead and get her a ring and we could plan a wedding. The only questions are, is will she dump Dean and marry me?

A/N: Please leave me a review. Please keep all reviews G rated with no bleeped out with stars, implied, or actual cuss words. Thanks! ;)


	3. Reading

Disclaimer: I do not own the Gilmore Girls show, books, characters, or any products or merchandise affiliated with it.

A/N: Here is a new chapter! Hehee! REVIEW! This is a strictly G rated story. I don't believe in pre-marital relations and none of that will be implied or included in any of my stories. Thanks.

I found that I, once again, could not concentrate on my book no matter how hard I tried. I have read the same paragraph over and over again, but the words never seem to penetrate my sub-coconscious. Of course I have tried to convince myself that it wasn't the fact that Jess was sitting about half a foot away from me. It had nothing to with the fact that I was head over heels in love with him and that I was the only one that knew about it… or so I think.

I find myself thinking about this Jess/Dean dilemma again. Honestly I just wish that he understood that I truly do love him but that I'm too scared of the unknown to give up my comfortable relationship with Dean.

Wow. I just admitted that I'm scared. I'm not scared of Jess or even of hurting Dean. I'm scared that if we date and we break up, which could be a strong possibility, since we are so very different, that I would lose him forever. I don't know if we could stay friends if I actually ever kissed him. Oh sure, Dean has his suspicions that I might have kissed Jess before, but in truth I haven't. I always knew that I was to scared to lose Dean to kiss Jess. Plus I'm not the cheating kind. The only way that I would ever kiss Jess is if I was single and got the guts to actually chance losing his friendship. And I don't know if I will ever be able to risk that.

I know that Jess seems like an 'I don't care about anything' kind of guy, but in reality he's not. The truth of the matter is, I think that Jess is truly scared to open up to other people. Underneath his sarcastic comments and tough act, he's scared. He has been hurt so many times it's hard for him to be himself around other people. But not me, I don't know why he has let me take a peek at his heart, but he has, and that is one of the reasons that I love him so much. He has truly been who he is with me. He is sensitive and nice. He is caring and kind. He love's to read just as much as I do. And I hope that he loves me just as much as I love him.

As I look at him sitting right beside me staring at the water, I wonder how much I hurt him everyday that I stay with Dean, when I know and that he knows that I don't truly love Dean. I stay with him because it's comfortable. Dean puts no demands on me. He doesn't challenge me to be a better person or to stand up for myself. My time is my own. The one thing that is his biggest fault and that annoys me so bad is the fact that he is madly jealous of Jess. And I suppose that that is reasonable. He can probably see what I am so bad at hiding. I love Jess. I don't know if anyone else realizes that, but I wonder if Dean truly does know. Maybe he just stays in a relationship with me, because it's comfortable. We hardly ever see one another. Really the only way you could say that we are boyfriend and girlfriend, is that we hang out and call ourselves that. Really we are friends and nothing more. I hardly ever even kiss Dean. Maybe it would be better to just dump him today. But where would that leave me? Without a so-called boyfriend and nothing to stop me from having a relationship with Jess. But can I date Jess? Can I truly risk our friendship? The same question comes to mind every time I think about this. Why am I not surprised?

As I think these last few thoughts, Jess senses my gaze upon him and slowly raises his head to smile at me. I give a small smile back and pick up my book once again.

A/N: What did you guys think? Please leave a review and let me know! Please keep all reviews clean and G rated. Thanks.


End file.
